Bromine → HCID 20260925, compound

HRID 1583374Notes

Reaction equation

HRID 1583374 reaction equation
[Br:1]Br.[C:3]([C:6]1[CH:7]=[CH:8][C:9]2[C:13]([CH3:14])=[C:12]([Br:15])[S:11][C:10]=2[CH:16]=1)(=[O:5])[CH3:4]>CCOCC.O1CCOCC1.O>[Br:15][C:12]1[S:11][C:10]2[CH:16]=[C:6]([C:3](=[O:5])[CH2:4][Br:1])[CH:7]=[CH:8][C:9]=2[C:13]=1[CH3:14]

Participants

6

Reactant 2

HCID 24408BromineHCID 20260923HCID 20260923, compound

Product 1

HCID 20260925HCID 20260925, compoundYield 85.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Bromine (1.67 g.) was added dropwise to a stirred solution of 6-acetyl-2-bromo-3-methylbenzo[b]-thiophene (2.50 g.) in a mixture of ether (15 ml.) and dioxan (15 ml.). The solution was stirred for 45 minutes and then diluted with water (100 ml.). The layers were separated and the aqueous layer was washed several times with ethyl acetate. The combined organic layer and extracts were washed with water and dried (Na2SO4). Evaporation of the solvent gave a solid which was chromatographed on silica gel. Elution with chloroform gave 2-bromo-6-bromoacetyl-3-methylbenzo[b]thiophene (2.75 g.) pure enough for further reaction. A sample crystallized from ethyl acetate/petrol (b.p. 60°-80°) had m.p. 126°-128° C.

Workup

  1. customThe layers were separated
  2. washthe aqueous layer was washed several times with ethyl acetate
  3. washThe combined organic layer and extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvent
  6. customgave a solid which
  7. customwas chromatographed on silica gel
  8. washElution with chloroform

Sources & evidence

ORD record
ord-63a8e6853a5d4e91a6f32145a7b7a74c
Source dataset
uspto-grants-1985_11
Patent number
US04551468

Reaction notes

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